P-Chloroacetophenone → Methyl 3-oxo-4-(4-chlorophenyl)butanoate

HRID 263644

반응식

HRID 263644 반응식
[C:1]([O:7][CH3:8])(=[O:6])[C:2](OC)=O.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=O)[CH3:17])=[CH:12][CH:11]=1.C[O-].[Na+].[Na].C([O-])(=[O:27])CCC>CO>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17](=[O:27])[CH2:2][C:1]([O:7][CH3:8])=[O:6])=[CH:12][CH:11]=1

참가 물질

7

반응물 5

HCID 7467P-ChloroacetophenoneHCID 11120Dimethyl oxalateHCID 104775ButyrateHCID 5360545SodiumHCID 10942334Sodium Methoxide

생성물 1

HCID 22246215Methyl 3-oxo-4-(4-chlorophenyl)butanoate

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Dimethyl oxalate (15.27 g, 0,129 mol), and 4'-chloroacetophenone (20.0 g, 0.129 mol) were added to methanol (300 mL). Sodium methoxide (25 wt. % in methanol, 70 mL) was added dropwise over about 0.5 hour. The reaction was stirred at room temperature for 16 hours, whereupon the sodium salt of the butanoate precipitated from solution. The mixture was treated with 70 mL of conc. HCl and the white suspension was stirred vigorously at room temperature for 1 hour. The suspension was cooled to 0° C. and held for 0.5 hour. The solid was filtered, and the filter cake was washed with cold water (100 mL). After drying in vacuo, methyl 4-[4-(chloro)phenyl]-3-ketobutyrate was obtained (16.94 g, 54.4%) as the enol: 1H NMR (CDCl3 /300 MHz) 8 7.94 (d, J=8.66 Hz, 2H), 7.48 (d, J=8.66 Hz, 2H), 7.04 (s, 1H), 3.95 (s, 3H), 3.48 (s, 1H).

후처리

  1. customprecipitated from solution
  2. additionThe mixture was treated with 70 mL of conc. HCl
  3. temperatureThe suspension was cooled to 0° C.
  4. waitheld for 0.5 hour
  5. filtrationThe solid was filtered
  6. washthe filter cake was washed with cold water (100 mL)
  7. customAfter drying in vacuo

출처 및 근거

ORD 기록
ord-fc6349c0750e4c6fae39c6f3f62f6318
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05643933

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